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Historicist: Toronto’s First Gangland Murder

The brutal death of bookie Jimmy Windsor shocks Toronto in 1939

The Toronto Telegram, January 9, 1939.

On the evening of Saturday, January 7, 1939, restaurant owner and illegal bookmaker Jimmy Windsor was just finishing his dinner along with his two half-sisters, their husbands, and his own girlfriend at his home at 247 Briar Hill Avenue. Following a knock at the door, Windsor’s half-sister Evelyn McDermott unwittingly admitted four men into the house who headed straight for Windsor, their faces reportedly hidden by handkerchiefs. After a brief exchange of words, the lead intruder produced a gun and began issuing Windsor instructions. When Windsor was slow to respond, he was shot in the groin and pushed toward the hall, relieved of the valuables on his body, and his body savagely beaten. The four unknown assailants soon fled, leaving Windsor to die in his own home. The next Monday, all three Toronto newspapers reported Windsor’s murder as the city’s first “gangland killing.”

Toronto’s underground betting culture had been well known for some time. In 1923, Ernest Hemingway wrote a feature on Toronto’s illegal gambling community for the Star Weekly, claiming that 10,000 people then placed bets in Toronto every day. Although Hemingway outlines a few betting scenarios in this piece, he noted that “the bulk of the bookmaking betting done in Toronto is done right in the offices, factories, or stores. Every office or building where any number of men are employed has its own bookmaking agent.”

By the late 1930s, illegal bookmaking was flourishing, and had led to some operations that were much larger and more organized. Jimmy Windsor had apparently operated as a bookmaker since the late 1920s, doing his business out of the White Spot Restaurant on Yonge Street, near Wellesley. Although known to the Toronto police and subject to at least one police raid, he had managed to stay out of trouble with the law, limiting his bookmaking to horse races, and usually receiving bets through agents rather than directly from the bettors. In What Happened to Mickey?, Toronto crime historian Peter McSherry notes that at this time, Toronto police often turned a blind eye to bookmaking and other “consensual vices… so long as they did not lead to bigger problems or there were no complaints that were persistent or could not otherwise be smoothed over.”

The Globe and Mail, January 9, 1939.

This laxity evaporated in the days following Windsor’s murder. There were no clear leads to either the motive or the identity of the assailants. Suspecting the murder was connected with the city’s underworld, the police began searching all the favourite locations of Toronto’s criminal classes. According to the Telegram, “gambling joints in the city and suburban area, poolrooms, and bootleggers were visited by detectives and, one by one, the men picked up began to arrive at [police] headquarters for questioning. The parade continued all Saturday night and all day Sunday.”

The newspapers circulated descriptions of the four wanted men as per the five eyewitnesses, although these were quite vague. None were said to be likely more than 30, and all four were described as having darker complexions. Windsor had evidently had some trouble from some Italians at his legitimate business, a dance hall called the Windsor Bar-B-Q, located near Yonge and Sheppard; this likely led to the suggestion that the gang of killers may have been Italian.

The media offered various theories as to the motive of the crime. Although Windsor was relieved of some valuable jewellery he had on him, it was not seen primarily as a robbery, as the men made no apparent effort to take other items of value which were in plain sight. The first theory to hit the newspapers was that Windsor had refused to pay money to a protection racket, with the suggestion that this racket was more of a problem in Toronto than had been previously believed. The Telegram wrote that “it was found that although tribute had been exacted and paid by many of the lesser fry of bookmakers and bootleggers, that the gang preying upon them were having more difficulty with the larger operators. According to the theory now held by the chief police investigators, the brutal murder was the gang’s way of telling them what they could expect.”

Scenes from Jimmy Windsor’s funeral. The Toronto Telegram, January 11, 1939.

A few days later, the Star reported on a tip suggesting that Windsor’s killers had come up from Buffalo specifically for the job, the motive being that Windsor had double-crossed a powerful gang. The Star continued trying to promote this theory, criticizing Toronto police for not working more actively with the Buffalo police and exploring this possibility. On January 16, they quoted Buffalo’s assistant chief of detectives as saying “we have several characters in Buffalo who are quite capable of the brutality that accompanied the killing… We are aware of a link between various rackets, including bookmaking and alcohol-running on both sides of the border.”

After a few weeks of speculation, no arrests had yet been made in Windsor’s murder. Several known Toronto underworld figures had appeared in police lineups before the five witnesses, but none had yet been identified. According to Peter McSherry, “the five eyewitnesses to Windsor’s death had made a secret agreement among themselves not to identify anyone in the line-up room,” lest a positive identification lead to their own murders to prevent them from testifying. As it was, the five witnesses to the murder remained under police protection at the Briar Hill Avenue house, reportedly afraid for their lives, and all three newspapers reported on the culture of fear that pervaded amongst all those who attended Windsor’s funeral.

The lack of an arrest made the Toronto media restless. All three newspapers, hungry for action, issued calls for the local police to clean up the gangs. One Globe and Mail editorial wrote that the murder was “symptomatic of the rotten condition that has been allowed to develop in Toronto. Its ramifications reach to other centres of the province, and apparently tie in with the mobsters in the United States.” Expressing the need for immediate action, the editorial added that “this city is not going to be made into a little Chicago by a crowd of tinhorn thugs.”

Evidence seized on an illegal bookmaker’s in Swansea. The Toronto Telegram, January 13, 1939.

In the week after Windsor’s murder, local police raided several larger betting establishments, both in Toronto and in the surrounding municipalities. One tip led to a raid of a parlor in Swansea, located above the Kingsway Pharmacy on Bloor, near Jane Street. The Globe and Mail wrote that “police are confident that it was the biggest bookmaking clearing house that has ever been uncovered in the province,” yielding eight arrests, 20 different telephones, and evidence that “the average betting for from one to three days would be $10,000.” Swansea’s police chief would later be fired after it was revealed that he had known about this bookmaking operation for several months, yet failed to act.

Toronto finally got some closure on the Windsor murder on February 23, when police formally charged Donald “Mickey” McDonald. McDonald had, in fact, been in custody for several weeks for his role in the assault and robbery of a Church Street bootlegger named James Elder. Out on bail during the time of the Windsor murder, he had subsequently been convicted for his role in the Elder case, and sent to Kingston Penitentiary.

Police were tipped to McDonald’s role in the Windsor murder by Jack Shea, an established criminal facing charges for a Port Credit bank robbery that he had executed with McDonald’s brother the previous December. Shea provided the police with some hearsay evidence, which led to McDonald’s inclusion in a lineup. The witnesses’ identifications of McDonald were imperfect to say the least, but apparently good enough to proceed to trial. For the Toronto media, however, the Windsor murder appeared to be solved, and attention soon shifted to Mickey McDonald.

Courtroom sketch drawn by Charles R. Snelgrove. The Toronto Telegram, February 24, 1939.

Although initially convicted, McDonald was able to successfully appeal following several irregularities, and was acquitted at the ensuing retrial. Having apparently escaped justice for one of Toronto’s most notorious murders, Mickey McDonald soon acquired a reputation as one of the country’s most notorious criminals. This reputation only grew when, while imprisoned for a truck hijacking, McDonald was part of a 1947 escape from Kingston Penitentiary. A few days after the escape, he and his two fellow escapees successfully held up a bank in Windsor.

Although both his confederates in escape were eventually found, McDonald was never positively identified again. In 1950, the Telegram quoted an unnamed Toronto police official as stating that the police “believe that Mickey was rubbed out by his own gunmen associates.” The article also claims that “Letters sent to local hoodlums from McDonald associates in the United States also tell of his violent death.” Over subsequent years, stories from the underworld repeated the assertion that McDonald had died, although accounts often disagreed on the location and the circumstance. By 1955, the belief that McDonald was dead was evidently shared by those in his old Toronto neighbourhood. The Globe and Mail’s Phil Jones interviewed people with connections to McDonald, and found someone who claimed McDonald was buried in New York after interfering with an established “dope racket.” “Officially,” Jones wrote, “Mickey is still alive. He will remain that way until his body is found. But to Jarvis St. he is dead.”

Additional material from: the Globe and Mail (January 9, January 10, January 11, January 12, January 13, January 14, January 16, January 25, February 17, February 24, February 25, 1939; January 6, 1955); Peter McSherry, What Happened to Mickey?: The Life and Death of Donald “Mickey” McDonald, Public Enemy No. 1 (Dundurn, 2013: Toronto); the Toronto Star (January 9, January 10, January 11, January 12, January 13, January 14, January 16, January 17, January 18, January 20, January 25, January 27, February 1, February 3, February 24, February 25, 1939); Star Weekly/em> (December 29, 1932); the Toronto Telegram (January 9, January 10, January 11, January 12, January 13, January 14, January 17, February 16, February 17, February 24, 1939; March 27, 1950; December 11, 1952).

Every Saturday, Historicist looks back at the events, places, and characters that have shaped Toronto into the city we know today.


  • Black_Fist

    I always find it amusing when I read articles like these then read most right wing publications act as if gang violence is a new phenomenon that just happen to rear its head around the same time as Trudeau sr. came to power. Such selective memory right wing history revisionists have. Ironically, those being racially profiled those times feel that it is their right to do so to new immigrants today.

    • nevilleross

      I agree. And, I want to know why these people can’t focus on the gang violence that comes from white biker gangs, when it happens.

      • Black_Fist

        Because when the greater public hears the term ‘gang members’ they automatically conjure up an image of a young black male in their heads. When the media covers black gang violence, they typically branch off to other discussions of single mothers, absentee fathers and other racist stereotypes which sparks their audiences’ attention (which usually consist of a particular demographic). People use these simplistic stereotypes to ‘rationalize’ their next to non existent understanding of gang violence. White bikers do not fit into what they deem as typical gangsterism. Bikers are not young, most of them are not from poor backgrounds and they do not necessarily come from single family homes. Trying to explain how white bikers fit in to the SAME drugs, guns and gangs phenomenon not only complicates what they deem a simplistic formula (poor, single parent, black kids=gangs) but it also shifts the focus off of the black community and makes them confront their own short comings, which up to this point, was the fault of rap music and Liberal socialists. They do not make laws that go after drug users, they go after dealers. They do not make laws that focus on the prostitutes, they focus on the pimps.

    • UrKiddingRite

      Yes limp everyone thinks it’s a new black thing. I mean AL Capone wasn’t a gangster who no-one ever heard about. Bugsy Siegel? Nope he was a milkman I think was he not? The James Younger Gang from the old west? Nope couldn’t be a gang cause they were white right? Jessie James’ gang? Butch Cassidy’s gang? Hell’s Angels? Rock Machine? Bandito’s? The lists go on and on.

      limp everyone knows that gangs have been around since forever and they have been violent since forever it’s just you that feel better about yourself when you say things like, “gang violence is a new phenomenon” because then you can add the race label to it and stoke those flames you like to see so much. The only difference is that with the about gangs, even though you like to pretend it doesn’t happen, is that the police are/were all over them all the time working at keeping them in check without reverends criticizing how they are focusing on minorities and not on the gangs. Like the gangs are not made up of people but are living breathing life forms that are made of up anything but people.
      Another fail for you.

      • Black_Fist

        Ah, so for once, you can admit that those Bikers are actually GANG BANGERS and NOT “motorcycle enthusiasts” or “organized criminals”. Nope. Just typical cocaine addicted, gang banging scum bags. So how come these gang banging scum bag Bikers are NOT indicative of the white community the way Bloods and Crips are for the black community (at least according to popular belief)?

        Diddles, when the black community was telling the police and politicians that if they carry on with their closet bigotry and heavy handed policing, that they will soon follow the steps of their AmeriKKKan counterparts all through out the mid 80s to early 90s, the greater public never gave a crap. As long as it happened in our communities, they didn’t care. Then some white girl gets killed on boxing day, NOW it’s EVERYBODIES problem. Nah….no bigotry there.

        & for the record, the police wasn’t all “over them” (the gangs) at first. Police were telling the public that Toronto didn’t have any gangs through out most of the 1990s. They said these “gangs” were nothing more than just some punk kids who watched too much TV. The police were more worried about their public image and perception than they were about addressing community concerns back then (as they are today). Police ignored the problem. They HAD the chance to catch youth gang violence as we know it in its infancy. NOW its entrenched in EVERY poor neighbourhood, and now EVERY kid from housing is a “gang member” or “gang affiliated”. A complete 360. I should know. I was there. Where were you?

        & for your info, Diddles, the reverends weren’t against police going after the gangs, they were more concerned with the fact that police couldn’t be bothered to differentiate between gang members and kids who were just in to fashion (a backwards baseball cap isn’t considered ‘gang attire’ when Justin Beiber look-a-likes wear them). But those are poor black folk concerns. Nothing you white boys have to worry. There’s that white privilege again.

        I find it funny how you honestly believe that black people somehow prosper by being the brunt of racial indifference or that we somehow enjoy being singled out. That is a complete and utter “fail” on YOUR part. Keep displaying your total ignorance and willful blindness to right wing bigotry, Diddles.

        • UrKiddingRite

          I finally admit that H/A’s are gang members??? Maybe you should try reading my comments instead of ranting and raving. I have always said that H/A’s are gang members…biker gang members…who deserve LONG prison sentences and no parole. I have never EVER thought of them as anything other than criminals and the fact that that just sunk into your head shows me that maybe you need to take off the “I See Racists Everywhere” glasses and actually read what I write.
          As for the H/A’s/Bloods/Crips being/not being indicative to their own societies. I think this has more to do with the differences between the societies. In Quebec the citizens finally had enough of the H/A violence and took to the streets demanding the police do something and then they stepped back and allowed the police to deal with the H/A – Rock Machine biker gangs in whatever manner the police deemed appropriate. Then you have Bloods/Crips and the citizens take to the streets demanding that the police do something about the gangs and then when the police come into their neighbourhood to start doing something they find those same citizens standing in the way of everything they do because the people they start arresting (harassing?) are their sons/daughters/nephews/nieces/cousins/uncles/aunts; so a week after taking to the streets demanding the police do something they take to the street again protesting what the police are doing.
          I suppose the biggest difference is that biker gangs have definite and defined members and prospects which make them easier to target where street gang members mostly have “colors” which can mean a gang member one second and “just a kid wearing a blue or red shirt” the next depending on the situation. I can’t believe I really have to explain that to you because, whenever there is a black kid murdered, you are the first one offended when someone calls them a gang member just from the clothes or hand signs the kid flashes, in the newspaper photo but if you stop and think about it for a second, you should be thinking, if the kid WASN’T a gang member why was he killed? And the reason usually comes back as??? That he was MISTAKEN for a gang member by another real gang member and murdered. So if the real gang members can’t tell the difference between other gang members and those “kids who are just dressed up and playing gang members” how would you expect the police to do it when they are just out patrolling the streets looking for “real” gang bangers? Please explain?
          “NOW its entrenched in EVERY poor neighbourhood, and now EVERY kid from housing is a “gang member” or “gang affiliated” – and this comment just shows your non-rational thinking. Here you say, from your own personal experience, that gang life is entrenched in the poor neighbourhoods and that EVERY kid is a gang member or gang affiliated which, to any rational person, would mean that when the police patrol those neighbourhoods stopping kids at random that they are more than likely stopping gang members and not some poor kids just playing in the streets like you (and the reverends) start ranting about in your next paragraph. How can it be both? How, in your mind, can “EVERY kid from housing is a “gang member” or “gang affiliated”” yet none of them are when they are murdered or when the police come around? I don’t get that. Please explain.
          “you honestly believe that black people somehow prosper by being the brunt of racial indifference or that we somehow enjoy being singled out.” – you are wrong with this (again) and it’s something that you made up yourself to refute my asking you questions. I am against racial indifference and certainly would not stand silently by while a black man or woman was singled out for humiliation or ridicule but that doesn’t mean that I will agree with or support everything they do or say. Disagreeing doesn’t make a person racist even though you believe otherwise.
          But since you mentioned racial indifference have you ever considered that it might come from white people being blamed for any and all problems, past and current, experienced for blacks (and natives) through the guise of “helping” that maybe it comes from white people backing off and not getting involved because everything has always been their fault in the past and now they’re thinking, “Whoa I am not touching this with a 10ft pole because white person’s “help” has never helped them in the past, and if fact made it worse, so now I’m just gonna stay out of it and let them figure it out for themselves. That way they can’t blame me if it all falls apart again.”
          You can spend your entire life pointing the finger at and blaming someone else for all your problems and then point your finger at them and blame them for not solving all the problems you say they caused. Or can you?

      • zozm

        Race is never an issue when they talk about biker gangs. You would never hear the phrase the ‘white biker gang/mafiosi from Toronto’s north end shot and paralyzed innocent bystander Louise Russo.’

        Ethnicity sometimes is when they talk about the mob. Although, in the last decade or two the media is reluctant to call them the Italian mafia. Yet, somehow, it’s important to note that black street gangs are black street gangs. As if being black somehow tells us something about them other than their skin pigmentation.

        Even if some black people like to scream and yell racism while they’re out dealing drugs and gang banging in an attempt to get the police off their back it doesn’t mean there isn’t a double standard when it comes to race, the prosecution of crime and the 90 something percent of the black population who are law abiding citizens.